Enrofloxacin (Ref: BAY VP 2674)

Enrofloxacin (Ref: BAY VP 2674)	Last updated: 18/05/2024
(Also known as: BRN 5307824)

GENERAL INFORMATION

Description

A broad-spectrum bactericidal antibiotic used in veterinary medicine

Availability status

Current

Introduction & key dates

Examples of veterinary uses

Used to treat domesticated animals for a variety of infections including E.coli., Enterobacter, Campylobacter, Shigella and Salmonella

Examples of species treated

Domestic animals including: Dogs, Cats, Rabbits, Horses. May also be used on Reptiles, Poultry, Swine and Cattle.

Approval status

VMR 2013/2033 approval status (GB/UK)

Approved

EU Regulatory approval status

Approved

Chemical structure

Isomerism

Chemical formula

C₁₉H₂₂FN₃O₃

Canonical SMILES

CCN1CCN(CC1)C2=C(C=C3C(=C2)N(C=C(C3=O)C(=O)O)C4CC4)F

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

SPFYMRJSYKOXGV-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C19H22FN3O3/c1-2-21-5-7-22(8-6-21)17-10-16-13(9-15(17)20)18(24)14(19(25)26)11-23(16)12-3-4-12/h9-12H,2-8H2,1H3,(H,25,26)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
enrofloxacin	-

General status

Veterinary substance type

Antibiotic, Chemotherapeutic agent, Medicinal drug, Bactericide

Substance groups

Fluoroquinolone

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Not clear but believed to act by inhibiting bacterial DNA gyrase

Molecular targets

[DNA gyrase subunit A, Antagonist], [DNA topoisomerase 2-alpha, Antagonist]

CAS RN

93106-60-6

EC number

CIPAC number

US EPA chemical code

PubChem CID

Therapeutic Class

Antiinfectants for systemic use: Antibacterials for systemic use

ATCvet Code

QJ01MA90

Controlled Drug?

Regulation 37/2010 MRL Classification

Allowed substance (Table 1: All food producing species)

Molecular mass

359.4

PIN (Preferred Identification Name)

IUPAC name

1,4-dihydro-1-cyclopropyl-7-(4-ethyl-1-piperazinyl)-6-fluoro-4-oxo-3-quinolinecarboxylic acid

CAS name

1-cyclopropyl-7-(4-ethyl-1-piperazinyl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Other status information

Relevant Environmental Water Quality Standards

Physical state

Pale yellow crystalline powder

Related substances & organisms

orbifloxacin

ciprofloxacin

marbofloxacin

Formulations

Property

Product

Manufacturer

Authorisation Route

Legal Class (GB/UK)

Example products (past and present) using this active

Baytril 10% Oral Solution

Elanco Europe Ltd

UK National authorisation

Prescription only medicine to be authorised by a veterinarian (POM-V)

Enrobactin Concentrate Oral Solution

LeVet Beheer B.V.

GB National authorisation

Prescription only medicine to be authorised by a veterinarian (POM-V)

Enrocat Suspension

Livisto International S.L.

GB National authorisation

Prescription only medicine to be authorised by a veterinarian (POM-V)

Lanflox Solution for Drinking Water

Vetpharma Animal Health S.L.

GB National authoristion

Prescription only medicine to be authorised by a veterinarian (POM-V)

Formulation and application details

Available in a variety of formulations including solutions for injection, tablets for oral use and oral suspensions

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

250

at 25 °C

Moderate

Solubility - In organic solvents at 20 °C (mg l⁻¹)

Melting point (°C)

220

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

Octanol-water partition coefficient at pH 7, 20 °C

5.01 X 10⁰⁴

Calculated

Log P

4.7

High

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

6.21

Vapour pressure at 20 °C (mPa)

2.53 X 10^-08

Low volatility

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

3.2 X 10^-08

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

Max @ 270+1nm and 314+2nm

Surface tension (mN m⁻¹)

Refractive Index

Environmental release

Identified in pig and poultry manure at high concentrations implying manure implying a major release route

Degradation

Property

Value

Source; quality score; and other information

Interpretation

Soil degradation (days) (aerobic)

DT₅₀ (typical)

123

Persistent

DT₅₀ (lab at 20 °C)

297

Persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

Note

DT₅₀ range 99-149 days, DT₉₀ range 330-495 days; Industry data DT₅₀ 359-696 days (R3)

Manure DT₅₀ (days)

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Note

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

Note

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

Air degradation

As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.

Decay in stored produce DT₅₀

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

Non-mobile

K_oc (mL g⁻¹)

392600

Notes and range

K_oc range 16506-768740 mL g⁻¹

Freundlich

K_f (mL g⁻¹)

K_foc (mL g⁻¹)

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-3.94

Calculated

Low leachability

Bio-concentration factor

BCF (l kg⁻¹)

CT₅₀ (days)

Known soil and groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

ciprofloxacin (Ref: BRN 3568352)

Animal (Urine and faecal)

enrofloxacin amide

Animal (Urine and faecal)

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

Birds - Acute LD₅₀ (mg kg⁻¹)

Birds - Short term dietary (LC₅₀/LD₅₀)

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

Soil micro-organisms

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Chronic

Bumblebees (Bombus spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Mason bees (Osmia spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Other bee species (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other bee species (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings)

Beneficial insects (Parasitic wasps)

Beneficial insects (Predatory mites)

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 10

Lepomis macrochirus

Moderate

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

~ 1

Pimephales promelas 7 day

Moderate

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

> 100

Daphnia magna

Low

Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

~ 1.0

Daphnia magna 48 hr

Moderate

Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

> 3

Ceriodaphnia dubia LC₅₀

Moderate

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

> 0.084

Lemna gibba

Moderate

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

> 2.6

Pseudokirchneriella subcapitata

Moderate

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

Mesocosm study data

NOEAEC mg l⁻¹

HUMAN HEALTH AND PROTECTION

General

Property

Value

Source; quality score; and other information

Interpretation

Threshold of Toxicological Concern (Cramer Class)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 35.47

Rat 4 hr

Other Mammal toxicity endpoints

Intravenous LD₅₀ = 200 mg kg⁻¹

Mouse

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

Mammalian dose elimination route and rate

Eliminated by both renal and hepatic metabolism

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

May cause gastrointestinal disturbances

Handling issues

Property

Value and interpretation

General

Light sensitive

CLP classification 2013

WHO Classification

Not listed (Not listed)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

enrofloxacin

French

enrofloxacine

German

Danish

Italian

Spanish

enrofloxacino

Greek

Polish

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	18/05/2024
Contact:	aeru@herts.ac.uk
Please cite as:	Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242